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Indole spiropyridino coumarin compound as well as preparation method and application thereof

An indole spiropyridine and coumarin technology, which is applied in the field of pesticides, can solve problems such as no research reports on indole spiropyridine coumarin compounds, and achieves high application potential, high research value, and good bacteriostasis. active effect

Active Publication Date: 2021-06-04
JIANGSU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no research report on indolespiropyridocoumarin compounds in the literature

Method used

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  • Indole spiropyridino coumarin compound as well as preparation method and application thereof
  • Indole spiropyridino coumarin compound as well as preparation method and application thereof
  • Indole spiropyridino coumarin compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] Weigh 0.21g (1.0mmol) N-methyl-5-nitroisatin, 0.17g (1.5mmol) 1,3-cyclohexanedione, 0.16g (1.0mmol) 4-aminocoumarin and 0.09g (0.5mmol) p-toluenesulfonic acid monohydrate (p-TSA.H 2 O) dissolved in 5 mL of water, heated to 80° C., stirred for 2 hours, cooled to room temperature, filtered to remove the solvent, dried, and recrystallized from methanol to obtain a yellow solid, that is, a compound having the structure of formula 1a. It was determined that the yield was 81%, m.p.>320°C. 1 H NMR (400MHz, DMSO-d 6 )δ:9.98(s,1H),8.43(dd,J=8.2,1.5Hz,1H),8.18(dd,J=8.6,2.4Hz,1H),7.94(d,J=2.4Hz,1H), 7.74-7.66(m,1H),7.54-7.47(m,1H),7.39(dd,J=8.4,1.2Hz,1H),7.15(d,J=8.7Hz,1H),3.24(s,3H) ,2.94-2.75(m,2H),2.27-2.13(m,2H),2.00-1.85(m,2H).Anal.Calcd for C 24 h 17 N 3 o 6 : C, 65.01; H, 3.86; N, 9.48. Found: C, 64.75; H, 3.95; N, 9.35.

Embodiment 2

[0024]

[0025] Weigh 0.19g (1.0mmol) N-methyl-5-methoxyisatin, 0.22g (2.0mmol) 1,3-cyclohexanedione, 0.16g (1.0mmol) 4-aminocoumarin and 0.08 g(0.4mmol)p-TSA.H 2 O was dissolved in 5 mL of water, heated to 90°C, stirred for 3 hours, cooled to room temperature, filtered to remove the solvent, dried, and recrystallized from a mixed solution of ethyl acetate and ethanol to obtain a yellow solid, namely the compound with the structure of formula 1b. It was determined that the yield was 82%, m.p.301.8-302.4°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 9.74(s, 1H), 8.38(d, J=7.8Hz, 1H), 7.68(t, J=7.6Hz, 1H), 7.47(t, J=7.7Hz, 1H), 7.37(d, J=8.3Hz,1H),6.79-6.69(m,2H),6.63(d,J=2.3Hz,1H),3.62(s,3H),3.10(s,3H),2.87-2.73(m,2H ),2.24-2.09(m,2H),1.97-1.82(m,2H).Anal.Calcd forC 25 h 20 N 2 o 5 H, 4.71; N, 6.54. Found: C, 69.94; H, 4.38; N, 6.28.

Embodiment 3

[0027]

[0028] Weigh 0.19g (1.0mmol) N-methyl-6-chloroisatin, 0.22g (2.0mmol) 1,3-cyclohexanedione, 0.16g (1.0mmol) 4-aminocoumarin and 0.06g ( 0.3mmol)p-TSA.H 2 O was dissolved in 5 mL of 1,2-dichloroethane, heated to 80°C, stirred for 10 hours, cooled to room temperature, filtered to remove the solvent, dried, recrystallized from ethanol and dichloromethane to obtain a yellow solid, which had the structure of formula 1c compound of. It was determined that the yield was 61%, m.p.>320°C. 1 H NMR (400MHz, DMSO-d 6 )δ:9.84(s,1H),8.38(dd,J=8.3,1.5Hz,1H),7.72-7.65(m,1H),7.51-7.45(m,1H),7.38(dd,J=8.4, 1.1Hz, 1H), 7.06-6.97(m, 2H), 6.87(dd, J=7.8, 1.9Hz, 1H), 3.14(s, 3H), 2.87-2.72(m, 2H), 2.26-2.10(m ,2H),1.97-1.81(m,2H).Anal.Calcd for C 24 h 17 ClN 2 o 4 H, 3.96; N, 6.47. Found: C, 66.85; H, 3.70; N, 6.70.

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Abstract

The invention belongs to the technical field of pesticides, and particularly relates to an indole spiropyridino coumarin compound as well as a preparation method and application thereof. According to the present invention, the isatin derivative, the 1, 3-dicarbonyl compound and the 4-aminocoumarin are adopted as the raw materials, the indole spiropyridino coumarin compound is synthesized through the one-pot method, and the indole spiropyridino coumarin compound has characteristics of unique chemical structure, higher research value and higher application potential. The preparation method provided by the invention has the advantages of cheap raw materials, simple process and strong universality, and is suitable for industrial production. Particularly, the method for preparing the indole spiropyridino coumarin compound by taking water as a solvent has the characteristics of being green, safe, efficient and environment-friendly. The indole spiropyridino coumarin compound provided by the invention has good bacteriostatic activity, has inhibitory activity on common plant pathogenic bacteria such as peanut brown spots, apple ring spots, wheat sheath blight, watermelon anthracnose and rice seedling, and has a potential application value.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to an indolespiropyridocoumarin compound and a preparation method and application thereof. Background technique [0002] Indolespiropyridine derivatives are heterocyclic compounds with multiple substitutions and multiple chiral centers, which mostly exist in natural products and have unique physiological and pharmacological activities. In view of its good biological activity and application prospects, organic chemists at home and abroad continue to develop its synthetic methods in order to more efficiently and greenly prepare indolespiropyridine derivatives for biological activity screening. Therefore, it is of great significance to find a green, safe, efficient and environmentally friendly preparation method and study its application for indolespiropyridine derivatives. At present, there is no research report on indolespiropyridocoumarin compounds in the literature....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/20A01N43/90A01P3/00
CPCC07D491/20A01N43/90
Inventor 仰榴青陈礼张敏夏梅赵婷
Owner JIANGSU UNIV
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